Cable M B, Jacobus J, Powell G L
Proc Natl Acad Sci U S A. 1978 Mar;75(3):1227-31. doi: 10.1073/pnas.75.3.1227.
The spin-labeled cardiolipin 1-(3-sn-phosphatidyl)-3-[1-acyl-2-(16-doxylstearoyl)glycero(3)phosphol]-sn-glycerol has been prepared. The stereoselective synthesis makes use of the monolysocardiolipin 1-(3-sn-phosphatidyl)-3-[1-acyl-2-lyso-sn-glycero(3)phospho]-sn-glycerol, available from the stereospecific hydrolysis of cardiolipin by phospholipase A2 (phosphatide 2-acylhydrolase, EC 3.1.1.4) of Trimeresurus flavoviridis. The results of treatment of the spin-labeled cardiolipin with the cardiolipin-specific phospholipase D (phosphatidylcholine phosphatidohydrolase, EC 3.1.4.4) (Hemophilus parainfluenzae) of known specificity and with phospholipase C (phosphatidylcholine cholinephosphohydrolase, EC 3.1.4.3) of Bacillus cereus are consistent with the assigned structure. The spin-labeled cardiolipin is further characterized and the unique features of this diastereomer are discussed in the context of the unusual stereochemistry of the natural phospholipid.
已制备出自旋标记的心磷脂1-(3 - sn - 磷脂酰)-3-[1 - 酰基 - 2-(16 - 二氧硬脂酰)甘油(3)磷脂]-sn - 甘油。该立体选择性合成利用了单溶血心磷脂1-(3 - sn - 磷脂酰)-3-[1 - 酰基 - 2 - 溶血 - sn - 甘油(3)磷酸]-sn - 甘油,其可通过竹叶青蛇的磷脂酶A2(磷脂2 - 酰基水解酶,EC 3.1.1.4)对心磷脂进行立体特异性水解获得。用已知特异性的嗜副流感嗜血杆菌的心磷脂特异性磷脂酶D(磷脂酰胆碱磷脂水解酶,EC 3.1.4.4)和蜡状芽孢杆菌的磷脂酶C(磷脂酰胆碱胆碱磷酸水解酶,EC 3.1.4.3)处理自旋标记的心磷脂的结果与所指定的结构一致。对自旋标记的心磷脂进行了进一步表征,并结合天然磷脂不寻常的立体化学对该非对映异构体的独特特征进行了讨论。